Best 5 Mens Sneakers in 2026

Make sure your men's street shoes can handle your adventures! Our Groveton mixed-media chukkas feature recycled materials, cushiony footbeds, and streamlined styling that's great dressed up or down.

ON THE TRAIL OR THE STREET, Timberland has the styles you'll love to wear. From ankle boots & sneaker boots to sandals & boat shoes, Timberland will keep you on your feet & looking fabulous.

TIMBERLAND HAS YOU COVERED whether you're looking for men's boots, women's boots, or kids boots. For the best in hiking boots, rain boots, work boots, casual shoes & boots & more, choose Timberland.

Upper made with Better Leather from an LWG Silver-rated tannery and 100% recycled CORDURA Ecomade canvas

Lace-up style

ReBOTL fabric lining

Make sure your men's street shoes can handle your adventures! Our Groveton mixed-media chukkas feature recycled materials, cushiony footbeds, and streamlined styling that's great dressed up or down.

ON THE TRAIL OR THE STREET, Timberland has the styles you'll love to wear. From ankle boots & sneaker boots to sandals & boat shoes, Timberland will keep you on your feet & looking fabulous.

TIMBERLAND HAS YOU COVERED whether you're looking for men's boots, women's boots, or kids boots. For the best in hiking boots, rain boots, work boots, casual shoes & boots & more, choose Timberland.

Upper made with Better Leather from an LWG Silver-rated tannery and 100% recycled CORDURA Ecomade canvas

Lace-up style

ReBOTL fabric lining

Chukka-inspired fashion sneaker featuring metal eyelets and branded leather patch at padded tongue

Upper made with Better Leather from an LWG Silver-rated tannery and 100% recycled CORDURA Ecomade canvas

Lace-up style

ReBOTL fabric lining

Make sure your men's street shoes can handle your adventures! Our Groveton mixed-media chukkas feature recycled materials, cushiony footbeds, and streamlined styling that's great dressed up or down.

ON THE TRAIL OR THE STREET, Timberland has the styles you'll love to wear. From ankle boots & sneaker boots to sandals & boat shoes, Timberland will keep you on your feet & looking fabulous.

TIMBERLAND HAS YOU COVERED whether you're looking for men's boots, women's boots, or kids boots. For the best in hiking boots, rain boots, work boots, casual shoes & boots & more, choose Timberland.

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Make sure your men's street shoes can handle your adventures! Our Groveton mixed-media chukkas feature recycled materials, cushiony footbeds, and streamlined styling that's great dressed up or down.

ON THE TRAIL OR THE STREET, Timberland has the styles you'll love to wear. From ankle boots & sneaker boots to sandals & boat shoes, Timberland will keep you on your feet & looking fabulous.

TIMBERLAND HAS YOU COVERED whether you're looking for men's boots, women's boots, or kids boots. For the best in hiking boots, rain boots, work boots, casual shoes & boots & more, choose Timberland.

Upper made with Better Leather from an LWG Silver-rated tannery and 100% recycled CORDURA Ecomade canvas

Lace-up style

ReBOTL fabric lining

Timberland Adventure 2.0 Chukka

Smooth Leather Uppers

Soft Breathable Textile Lining

Everyday adventures call for this versatile chukka boot

Premium nubuck leather and CORDURA® EcoMade canvas upper

Defender Repellent Systems® upper treatment repels water and stains

Everyday adventures call for this versatile chukka boot

Premium nubuck leather and CORDURA® EcoMade canvas upper

Defender Repellent Systems® upper treatment repels water and stains

Upper Material: leather

Lining: mesh

Closure: lace

Our Davis Square mixed-media chukkas are made to feel comfy inside with lightweight OrthoLite footbeds and look great outside with Defender Repellent Systems treatment to help repel stains. They're also mindfully made with responsibly sourced leather and eco-conscious fabric.

Upper: Better Leather from a tannery rated silver by the Leather Working Group for its water, energy, and waste management practices, and Cordura Ecomade canvas

Defender Repellent Systems treatment

Upper made with Better Leather from an LWG Silver-rated tannery and 100% recycled CORDURA Ecomade canvas

Lace-up style

ReBOTL fabric lining

Collection: Oxford sneakers

Men's sneakers

Comfortable trainers

Timberland Adverntue 2.0 Cupsole

Smooth Leather Uppers

Soft Breathable Textile Lining

Premium nubuck upper with suede collar

Breathable 50% recycled PET mesh lining

Removable, textile lined, foam insole

Chukka-inspired fashion sneaker featuring metal eyelets and branded leather patch at padded tongue

Slip-on fashion sneaker with elastic goring at opening featuring stud details on lateral side and contrast trim around topline

50% organic cotton/50% cotton canvas upper panels for lightweight comfort and durability

50% recycled PET lining is comfortable, breathable, and environmentally conscious

100% cotton canvas upper for lightweight comfort and durability

Lace-up style for a secure, adjustable fit

50% recycled pet mesh lining is comfortable, breathable and environmentally conscious

Upper made with Better Leather from an LWG Silver-rated tannery

Padded collar

Mesh lining

Upper made with Better Leather from an LWG Silver-rated tannery

Padded collar

Mesh lining

Upper made with Better Leather from an LWG Silver-rated tannery

Padded collar

Mesh lining

Upper material made with Tencel Lyocell and Refibra technology fabric

100% cotton laces

Mesh lining

The Timberland 6-Inch Premium Waterproof Boot “Wheat” is an all-time classic colorway of the rugged workwear boot that is worn by all walks of life

A classic cold weather footwear style, Timberland’s 6-Inch Waterproof Boot is durable, water-resistant, and effortlessly timeless

It’s a boot that’s appeared in hip-hop music videos, on construction sites, and in city streets, since forever

Inner material: Rebotl

Sole: rubber

Closure: lacing

Premium waterproof leather with waterproof membrane for extreme abrasion resistance and dry feet